35925-21-4

Basic information

• Product Name: L-Tryptophan, 5-oxo-L-prolyl-L-histidyl-
• Synonyms: L-Tryptophan,5-oxo-L-prolyl-L-histidyl
• CAS NO: 35925-21-4
• Molecular Formula: C22H24N6O5
• Molecular Weight: 452.47
• Mol File: 35925-21-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 1072.7±65.0 °C(Predicted)
• Density: 1.456±0.06 g/cm3(Predicted)
• CAS DataBase Reference: L-Tryptophan, 5-oxo-L-prolyl-L-histidyl-(CAS DataBase Reference)
• NIST Chemistry Reference: L-Tryptophan, 5-oxo-L-prolyl-L-histidyl-(35925-21-4)
• EPA Substance Registry System: L-Tryptophan, 5-oxo-L-prolyl-L-histidyl-(35925-21-4)

Safety Data

• Hazardous Substances Data: 35925-21-4(Hazardous Substances Data)

Usage

Description

L-Tryptophan, 5-oxo-L-prolyl-L-histidyl-, also known as L-Pyroglu-L-His-L-Trp, is a compound that serves as an impurity in Leuprolide (L330590), a medication used for various therapeutic purposes. L-Tryptophan, 5-oxo-L-prolyl-L-histidylis derived from the combination of three amino acids: L-tryptophan, L-proline, and L-histidine, and is characterized by its unique structure and properties.

Uses

Used in Pharmaceutical Industry:
L-Tryptophan, 5-oxo-L-prolyl-L-histidylis used as an impurity in the production of Leuprolide, which is a medication for the treatment of central precocious puberty. It plays a role in the synthesis of drugs that are useful for treating endometriosis, hysteromyoma, and premenopausal breast cancer.
Leuprolide is a gonadotropin-releasing hormone (GnRH) agonist that works by suppressing the production of sex hormones, such as estrogen and progesterone, in the body. This suppression helps in managing the symptoms and progression of the aforementioned conditions.

Upstream product

• 33515-09-2 gonadorelin 
• 33515-09-2 gonadotropin releasing hormone 
• 76712-82-8 histrelin 

Downstream Products

• 84636-31-7 C₆₃H₇₀N₁₀O₁₁ 

Relevant articles and documents

Degradation kinetics of gonadorelin in aqueous solution

The degradation kinetics of gonadorelin were investigated systematically with reversed-phase high-performance liquid chromatography. The stability- indicating properties of this system were checked with photodiode array detection and by comparison with capillary zone electrophoretic analysis. Influences of gonadorelin concentration, pH, temperature, buffer ions, and ionic strength on the degradation kinetics were studied. The pH-Iog κ(abs) profile can be divided into three pads, a proton, a solvent, and a hydroxyl- catalyzed section, with different degradation products. These degradation products were characterized by mass using LC-MS. Gonadorelin is most stable at pH 5-5.5 with a half-life of 70 days at 70 °C. The overall degradation rate constant as a function of the temperature under acidic and alkaline conditions obeys the Arrhenius equation. The gonadorelin concentration and the concentrations of acetate, phosphate, borate, and carbonate buffer have no influence on the decomposition rate of the κ(abs). Increasing ionic strength led to higher κ(abs) at pH 2 and lower κ(abs) at pH 9, but influences were relatively small.

Characterization of the degradation products of luteinizing hormone releasing hormone

The degradation products of luteinizing hormone releasing hormone [LH/RH; 1; gonadorelin releasing hormone (GnRH); 2] were determined in aqueous solution (pH 6.5) at 25, 37, 50, and 80 °C. The predominant route of degradation involved the cleavage of the 2 to the free acid form in peptides 4 and 10. Racemization of the serine and histidine residues to give peptides 2 and 3 was a second route of degradation.